Reaction equation
COC1C=CC([C@@H]([NH:11][C@@H:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)C)=CC=1.FC(F)(F)C(O)=O.CC1C(C)=C(C)C(C)=C(C)C=1>>[NH2:11][C@@H:12]1[C:20]2[C:15](=[CH:16][C:17]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][CH:19]=2)[CH2:14][CH2:13]1Participants
4
Conditions
- Temperature
- 70 °C
Procedure
To 452 mg of methyl (1S)-1-{[(1S)-1-(4-methoxyphenyl)ethyl]amino}indane-5-carboxylate were added 34 ml of trifluoroacetic acid and 1.03 g of pentamethylbenzene, followed by stirring at 70° C. for 4 days, and the solvent was evaporated under reduced pressure. To the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution and chloroform to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 165 mg of methyl (1S)-1-aminoindane-5-carboxylate.
Workup
- customthe solvent was evaporated under reduced pressure
- additionTo the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution and chloroform
- customa layer separation operation
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-7346f4a4800a40d8af71c4b993c44102
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447090B2
Linked notes
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